- Amidoamine double tailed cationic surfactant based on dimethylaminopropylamine: Synthesis, characterization and evaluation as biocide
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Three amidoamine cationic surfactants with double tailed were prepared and their chemical structures was confirmed using spectroscopic analysis like FTIR and 1H NMR. The surface parameters of the amidoamine surfactants were determined from surface tension and conductance measurements. The double tailed amidoamine surfactant shown low critical micelle concentration than conventional surfactants with their dependence on chain length and temperatures. Thermodynamic parameters clarified the tendency of surfactants to adsorb at interface than to form micelle and both of the two processes depend on the alkyl chain and temperature. The prepared surfactants were evaluated against microorganism showing that they have good biological activity against both Gram positive and negative bacteria but they have no effect on fungi.
- Shaban, Samy M.,Aiad, Ismail,Fetouh, Howida A.,Maher, Amr
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- Design, synthesis, antibacterial activity and toxicity of novel quaternary ammonium compounds based on pyridoxine and fatty acids
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A diverse series of 43 novel “soft antimicrobials” based on quaternary ammonium pyridoxine derivatives which include six-membered acetals and ketals of pyridoxine bound via cleavable linker moieties (amide, ester) with a fragment of fatty carboxylic acid was designed. Nine compounds exhibited in vitro promising antibacterial activity against Gram-positive and Gram-negative bacterial strains with MIC values comparable with reference antiseptics miramistin, benzalkonium chloride and chlorohexidine. On various clinical isolates, the lead compounds 6i and 12a exhibited antibacterial activity comparable with that of benzalkonium chloride while higher than that of miramistin. Moreover, 6i and 12a were able to kill bacteria embedded into the matrix of mono- and dual species biofilms. The treatment of bacterial cells by either 6i and 12a lead to fast depolarization of the membrane suggesting that the membrane is an apparent molecular target of compounds. 6i and 12a were non mutagenic neither in SOS-chromotest nor in Ames test and non-toxic in vivo at acute oral (LD50 > 2000 mg/kg) and cutaneous administration (LD50 > 2500 mg/kg) on mice. Taken together, our data allow suggesting described active compounds as promising starting point for the new antibacterial agents development.
- Agafonova, Mariya N.,Chirkova, Milana N.,Druk, Anastasia Y.,Grishaev, Denis Y.,Kayumov, Airat R.,Kazakova, Renata R.,Krylova, Elena S.,Nikishova, Tatyana V.,Nikitina, Elena V.,Sabirova, Alina E.,Sapozhnikov, Sergey V.,Shtyrlin, Nikita V.,Shtyrlin, Yurii G.
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- A lycine amphoteric surface active agent and its preparation method
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The invention discloses a glycine betaine-type ampholytic surfactant and a preparation method thereof. The preparation method of the glycine betaine-type ampholytic surfactant comprises the following steps of (1) amidation reaction: carrying out amidation reaction on natural fatty acid and 3-dimethylaminopropylamine under the action of a catalyst, and timely removing water generated through reaction by using a 4A molecular sieve to obtain alkylamid-propyl dimethyl tertiary amine; and (2) quaterisation reaction: carrying out quaterisation reaction on alkylamid-propyl dimethyl tertiary amine and sodium chloroacetate in a solvent to obtain the glycine betaine-type ampholytic surfactant. The ampholytic surfactant group contains an amido bond, the performance of the molecule is changed, the glycine betaine-type ampholytic surfactant has better foam stability and mild performance, and the emulsifiability is obviously superior to that of the glycine betaine-type ampholytic surfactant. The preparation method is simple in process and low in production cost; the raw materials are green and natural; the water generated in the amidation reaction process is absorbed through the 4A molecular sieve; and the yield is improved.
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Paragraph 0059; 0061
(2018/10/02)
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- A method for reducing betaine free acid in the process method of the (by machine translation)
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This invention discloses a method for reducing free acid betaine in the process, firstly on the fatty acid with a batch of reaction distilled N, N - dimethyl - 1, 3 - propanediamines waste liquid reaction, then in the system by adding pure N, N - dimethyl - 1, 3 - propylene diamine reaction, to obtain the intermediate alkyl amide propyl dimethylamine, then the alkyl amide propyl dimethylamine and chloroethyl acid reaction, to prepare amide propyl betaine, reduces the betaine in the free acid. Compared with the prior art, the present invention through improved technology, the repeated use of reflux, the raw material is improved N, N - dimethyl - 1, 3 - propanediamines utilization rate, through the added raw materials under high temperature conditions N, N - dimethyl - 1, 3 - propylene diamine, reflux circulating reflux use, not only promote the condensation reaction degree, reduce the consumption of the raw materials, so that the content of free acid in the product is reduced, improving the product quality, and reduce environmental pollution, and improves the economic problem of cost-effectiveness, favorable to commercial production. (by machine translation)
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Paragraph 0029; 0030; 0031
(2017/11/08)
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- N-(3-(Dimethyl benzyl ammonio)propyl)alkanamide chloride derivatives as corrosion inhibitors for mild steel in 1 M HCl solution: Experimental and theoretical investigation
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The effects of N-(3-(dimethyl benzyl ammonio)propyl)lauramide chloride (DMBL), N-(3-(dimethyl benzyl ammonio)propyl)myristamide chloride (DMBM) and N-(3-(dimethyl benzyl ammonio)propyl)palmitamide chloride (DMBP) on the corrosion of mild carbon steel in acidic medium (1.0 M HCl) were investigated using weight loss and electrochemical measurements. The inhibition efficiency was found to be hydrophobicity- and temperature-dependent. Increasing the hydrophobic chain length increased the efficiency due to greater adsorption on the metal surface. The inhibition efficiency is directly proportional to the tested temperature. The electrochemical polarization study revealed that the tested cationic surfactants are mixed-type inhibitors. The Villamil adsorption isotherm is the better-fitted model for describing the adsorption process on the selected steel in 1.0 M HCl medium. The change in the free energy of adsorption of the synthesized cationic surfactants on the metal surface indicates that the adsorption process is chemisorption. Double-layer capacitance values obtained from electrochemical impedance spectroscopy decrease in the presence of the synthesized surfactant. Quantum chemical calculations support the experimental data and the adsorption on the metal surface.
- Shaban, Samy M.
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p. 39784 - 39800
(2016/05/24)
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- Surface Parameters and Biological Activity of N-(3-(Dimethyl Benzyl Ammonio) Propyl) Alkanamide Chloride Cationic Surfactants
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Three cationic surfactants containing amide groups were prepared by quaternization of dimethylaminopropylamine with benzyl chloride. FTIR and 1H-NMR spectroscopy were used to confirm the chemical structure of the prepared cationic surfactants. The surface parameters were estimated using surface tension measurements at three different temperatures. The prepared cationic surfactant showed a lower CMC than conventional cationic surfactants. Thermodynamic parameters of adsorption and micellization depend mainly of alkyl chain length and temperature. The adsorption process is more favorable than micellization. The biological activity of the three surfactants was estimated using inhibition zone showing that amidoamine cationic surfactants have good activity and the surfactants C12Bn is the most effective one.
- Shaban, Samy M.,Aiad, Ismail,Ismail, Abdallah R.
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p. 501 - 510
(2016/05/02)
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- Synthesis and biological evaluation of novel aliphatic amido-quaternary ammonium salts for anticancer chemotherapy: Part II
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A series of novel aliphatic amido-quaternary ammonium salts were synthesized and evaluated for their anticancer effects involving induction of RhoB. Most of these compounds, featuring open-ring forms of aliphatic amido-quaternary ammonium salts, exhibited potent anti-proliferative activities in human cancer cell lines, including PC-3, NUGC-3, MDA-MB-231, ACHN, HCT-15, and NCI-H23. In further evaluation, the representative compound N,N-diethyl-N-(2-(N-methyltetradecanamido)ethyl)prop-2-en-1-aminium bromide (3b) exhibited potent pro-apoptotic activity, through RhoB activation, in HeLa cells.
- Yang, Jee Sun,Song, Doona,Ko, Won Jin,Kim, Bunyea,Kim, Bo-Kyung,Park, Song-Kyu,Won, Misun,Lee, Kiho,Lee, Kyeong,Kim, Hwan Mook,Han, Gyoonhee
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p. 621 - 628
(2013/07/27)
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- Synthesis and antibacterial activity of novel amido-amine-based cationic gemini surfactants
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A series of novel cationic gemini surfactants were synthesized from corresponding amido-amines in a single step reaction. The amido-amines were obtained from long chain carboxylic acids and 3-N,N-dimethylamino-1-propyl-amine with excellent isolated yield (up to 95 %). All the synthesized quaternary ammonium compounds (QACs) were further investigated for surface active properties. The critical micelle concentration (CMC) and the effectiveness of surface tension reduction were determined. The surface tension measurements of newly synthesized gemini surfactants showed good water solubility, and low CMC values, had great efficiency in lowering the surface tension and a strong adsorption at the air/water interface than the corresponding monomeric surfactants. Further, the antibacterial activity of the synthesized QACs against both Gram-positive and Gram-negative bacteria was also investigated.
- Ghumare, Anant K.,Pawar, Balu V.,Bhagwat, Sunil S.
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- Empirical correlations between krafft temperature and tail length for amidosulfobetaine surfactants in the presence of inorganic salt
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Long-chain amidosulfobetaine surfactants, 3-(N-fattyamidopropyl-N,N- dimethyl ammonium) propanesulfonates (n-DAS, n > 18), are insoluble in pure water due to their high Krafft temperature (TK), while they are soluble when inorganic salt is added to the surfactant solution as the T K of these zwitterionic surfactants is decreased. The influence of the salt content and ionic species of the added electrolytes on the T K of the series of amidosulfobetaine surfactants was examined by means of UV-vis spectrophometry and visual inspection. It was found that the TK of these surfactants depends strongly on not only the hydrophobic alkyl length (n), but also the salinity of the aqueous environment. When the salt concentration is increased from 0 to 100 mM, the TK shows a sharp decrease; when the salinity is fixed between 100 and 2000 mM, the T K varies linearly with n with a slope of ~7.7 irrespective of the salt species and the salt content. When the salt concentration is further increased above 2000 mM, a linear function is still observed, but the slope increases slightly.
- Chu, Zonglin,Feng, Yujun
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experimental part
p. 1175 - 1181
(2012/06/04)
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- Dimer poly-quaternary compounds
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The present invention relates to a novel class of polymeric compounds having specific quaternized amine based upon a dimer acid reacted with an dimethyl amino propyl amine to make an amido amine, which is subsequently reacted to make a polymeric quaternary compound. Dimer acid is a C-36 diacid having a cyclic structure and two amine groups that allow for the synthesis of a high molecular weight cationic compound which is extremely substantitive to human skin and are well tolerated by human tissue making them suitable for use preparation of barrier products for personal care applications.
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Page/Page column 9
(2008/06/13)
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- Use of amidoamines in ophthalmic compositions
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The use of certain amidoamines to disinfect contact lenses and preserve ophthalmic compositions is described, Ophthalmic compositions containing these compounds as disinfecting agents or preservatives are also described, The amidoamines utilized in the present invention have potent antibacterial and antifungal activity, and are chemically compatible with inorganic ions and other materials utilized in ophthalmic compositions.
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- Use of amidoamines in ophthalmic compositions
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Certain amidoamines, the use of same for disinfecting and cleaning contact lenses and preserving ophthalmic products, and associated ophthalmic compositions are described.
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- Process for the synthesis of esters and amides of carboxylic acids
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The invention relates to the preparation of an ester or an amide from an anhydride with an alcohol or an amine, wherein the anhydride is first prepared by reacting an acid and an alkyl chloroformate in a 100% aqueous medium, that is, 100% water.
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